Usage

flickruper uploads a single directory at once, without recursion
into subdirectories. It cannot upload a single file or several files.
This may change in the future.

First, place all your photos inside a dir, and, optionally, rename it to
how you want your resulting Flickr set to be named.

Then just

flickruper DIRNAME

If the set exists, it won’t upload the same file several times.

If you want tags, and/or other set name, do

flickruper DIRNAME --setname 'Custom set name' --tags 'Tag1 Tag2'

See –help for other options

flickruper --help

Note:

At first launch, flickruper requires a browser to get a token. If you
want to use it on a headless server, launch it first on your desktop,
get the token, and copy the ~/.flickr directory to your server.